p-Chlorothiophenol → 5-[(4-Chlorophenyl)sulfanyl]-2-thiophenecarbaldehyde

HRID 2301861Notes

Reaction equation

HRID 2301861 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[C:12]1[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=1>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:12]2[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 70621945-[(4-Chlorophenyl)sulfanyl]-2-thiophenecarbaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60%, 1.2 g, 30 mmol) is added to a solution of 4-chlorothiophenol (4.3 g, 30 mmol) in THF (30 mL). The resulting solution is stirred for 10 minutes then the solvent is removed in vacuo. Acetone (60 mL) is added followed by 5-bromothiophene-2-carboxaldehyde (3.0 mL, 25 mmol). The mixture is stirred at room temperature for 2 hours. The solvent is removed in vacuo and the resulting slurry diluted with CH2Cl2. This solution is washed three times with 1N NaOH then dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash column chromatography (gradient of 1 to 5% EtOAc in heptane) to give the desired product (6.2 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.13, 7.31-7.39, 7.63, 9.78.

Workup

  1. customthe solvent is removed in vacuo
  2. additionAcetone (60 mL) is added
  3. stirringThe mixture is stirred at room temperature for 2 hours
  4. customThe solvent is removed in vacuo
  5. additionthe resulting slurry diluted with CH2Cl2
  6. washThis solution is washed three times with 1N NaOH
  7. dry with materialthen dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by flash column chromatography (gradient of 1 to 5% EtOAc in heptane)

Sources & evidence

ORD record
ord-d5f5e306526a434297fe363d4730d719
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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